Ammonium Acetate → N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamide

HRID 72347

Reaction equation

HRID 72347 reaction equation
[C:1]([NH:5][S:6]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+].C([BH3-])#[N:25].[Na+]>CO>[C:1]([NH:5][S:6]([CH2:9][CH:10]([NH2:25])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 68288463N-(tert-Butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide

Product 1

HCID 68287917N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamideYield 105.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(tert-butyl)-2-(4-fluorophenyl)-2-oxoethanesulfonamide (657 mg), ammonium acetate (1.85 g) and sodium cyanoborohydride (166 mg) was stirred in methanol (12 ml) at 60° C. for 17 hours. The reaction solution was concentrated by rotary evaporation and the residue was taken up in ethyl acetate (50 ml). Then it was washed with 0.5 N aqueous sodium hydroxide solution (50 ml) and with saturated sodium chloride solution (50 ml), and the organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. This gave the product (697 mg) with a molecular weight of 274.3 g/mol (C12H19FN2O2S), MS (ESI): m/e=275 (M+H+).

Workup

  1. concentrationThe reaction solution was concentrated by rotary evaporation
  2. washThen it was washed with 0.5 N aqueous sodium hydroxide solution (50 ml) and with saturated sodium chloride solution (50 ml)
  3. dry with materialthe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e6e383aa11d742978b08a562cc141a0b
Source dataset
uspto-grants-2014_09
Patent number
US08828995B2

Linked notes

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